Methanol → (R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

HRID 418488Notes

Reaction equation

HRID 418488 reaction equation
[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[CH:6]=[CH:5]2.CO.C(N(CC)CC)C.Cl.[NH2:26][C@H:27]([CH3:31])[C:28]([NH2:30])=[O:29]>>[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:26]([C@H:27]([CH3:31])[C:28]([NH2:30])=[O:29])[CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 2775814(2R)-2-Aminopropanamide hydrochlorideHCID 595157256-Chloro-5-nitro-1H-isochromen-1-one

Product 1

HCID 59515858(R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Conditions

Temperature
55 °C

Procedure

To a solution of 6-chloro-5-nitro-1H-isochromen-1-one (950 mg, 0.0042 mol) in methanol (30 mL, 0.7 mol) was added triethylamine (0.64 mL, 0.0046 mol) and (R)-2-aminopropanamide hydrochloride (0.58 g, 0.0046 mol). The reaction was heated to 55° C. overnight and the solvent was removed under reduced pressure. The residue was purified by flash chromatography to afford the product as light yellow solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ad4264adc4504056827fada3c9089b58
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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